Diisopropyl Ether → (4-aminophenyl)(imino)methyl-lambda6-sulfanone

HRID 1891060Notes

Reaction equation

HRID 1891060 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[NH:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.C(OC(C)C)(C)C>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH3:13])(=[NH:12])=[O:11])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 7914Diisopropyl EtherHCID 12463933S-Methyl-S-(4-nitrophenyl)sulfoximine

Product 1

HCID 59674054(4-aminophenyl)(imino)methyl-lambda6-sulfanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2.45 g (12.2 mmol) of (RS)—S-(4-nitrophenyl)-S-methyl sulfoximide in 150 ml of ethanol is hydrogenated at room temperature with use of 0.80 g of Pd/C (10%×50% H2O) under a hydrogen atmosphere at normal pressure over 4 hours. The hydrogen absorption is 920 ml. The batch is filtered and concentrated by evaporation. The residue that is obtained is digested with diisopropyl ether. 1.90 g (11.2 mmol, corresponding to 92% of theory) is obtained.

Workup

  1. customThe hydrogen absorption
  2. filtrationThe batch is filtered
  3. concentrationconcentrated by evaporation
  4. customThe residue that is obtained
  5. custom1.90 g (11.2 mmol, corresponding to 92% of theory) is obtained

Sources & evidence

ORD record
ord-7ef199ea8fe1431cb772fbc19952981d
Source dataset
uspto-grants-2013_08
Patent number
US08507510B2

Reaction notes

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